KR20230096688A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound of Formula 1 and an organic light emitting device including the same.

Description

Compound and organic light emitting device including the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present specification relates to a compound and an organic light emitting device including the same.

In this specification, an organic light emitting device is a light emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material. The organic light emitting device can be roughly divided into two types according to the operation principle as follows. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as a current source (voltage source) It is a light emitting device of the form. The second is a type of light emitting device that injects holes and/or electrons into the organic semiconductor material layer forming the interface with the electrodes by applying voltage or current to two or more electrodes and operates by the injected electrons and holes.

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device. can lose In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows. Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials, depending on their functions. Light-emitting materials include blue, green, and red light-emitting materials according to light-emitting colors, and yellow and orange light-emitting materials required to realize better natural colors.

In addition, in order to increase color purity and increase light emitting efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The principle is that when a small amount of a dopant having a smaller energy band gap and higher luminous efficiency than the host constituting the light emitting layer is mixed in the light emitting layer in a small amount, excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength range of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.

In order to fully exhibit the excellent characteristics of the organic light emitting device described above, materials constituting the organic material layer in the device, such as hole injection materials, hole transport materials, light emitting materials, electron suppression materials, electron transport materials, electron injection materials, etc. are stable and efficient materials. Supported by this, the development of new materials is continuously required.

International Patent Publication No. 2017-126443

In this specification, a compound and an organic light emitting device including the same are described.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

R1 is hydrogen; heavy hydrogen; tritium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 is an integer from 0 to 8;

When n1 is 2 or more, R1 are the same as or different from each other,

L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing O or S,

At least one of Ar1 and Ar2 is of Formula 2 or 3 below,

[Formula 2]

[Formula 3]

In Formulas 2 and 3,

The dotted line is the part connected to L1 or L2,

R2 is hydrogen; heavy hydrogen; tritium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted heterocyclic group containing O or S,

r2 is an integer from 0 to 7, and when r2 is 2 or more, R2 are the same as or different from each other;

n1 is 0, or both R1 are hydrogen; tritium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or when it is a substituted or unsubstituted heterocyclic group, at least one of Ar1, Ar2, L1 and L2 is substituted with deuterium.

Another embodiment is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

The compound of the present invention can be used as a material for an organic material layer of an organic light emitting device. In the case of manufacturing an organic light emitting device including the compound of the present invention, an organic light emitting device having high efficiency, low voltage and long lifespan characteristics can be obtained, and when the compound of the present invention is included in the light emitting layer of the organic light emitting device, a high color gamut can be obtained. It is possible to manufacture an organic light emitting device having

1 and 2 show an example of an organic light emitting device according to the present invention.

Hereinafter, the present specification will be described in more detail.

In the present specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

Examples of substituents in the present specification are described below, but are not limited thereto.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, a position where the substituent is substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.

In this specification, the term "substituted or unsubstituted" means deuterium; tritium; halogen group; Cyano group (-CN); Silyl group; boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; and a substituted or unsubstituted heterocyclic group, which is substituted with one or two or more substituents selected from the group consisting of two or more substituents among the substituents exemplified above, or a substituent in which two or more substituents are connected. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

Examples of the substituents are described below, but are not limited thereto.

In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

In the present specification, the silyl group may be represented by a chemical formula of -SiY1Y2Y3, wherein Y1, Y2 and Y3 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. don't

In the present specification, the boron group may be represented by a chemical formula of -BY4Y5, wherein Y4 and Y5 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, a phenyl boron group, and the like.

In the present specification, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkyl arylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; Biphenylamine group; an anthracenylamine group; 9-methylanthracenylamine group; diphenylamine group; ditolylamine group; N-phenyltolylamine group; triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group and the like, but are not limited thereto.

In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.

In the present specification, the alkyl group of an alkylamine group, an N-arylalkylamine group, an alkylthioxy group, an alkylsulfoxy group, and an N-alkylheteroarylamine group is the same as the above-mentioned alkyl group. Specifically, the alkylthioxy group includes a methylthioxyl group; Ethylthioxy group; tert-butyl thioxy group; Hexylthioxy group; and octylthioxy group, and the alkyl sulfoxy group includes mesyl; ethyl sulfoxy group; propyl sulfoxy group; Butyl sulfoxy group and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, and the like. However, it is not limited to these.

In the present specification, the arylene group is the same as defined in the above aryl group except that it is a divalent group.

According to an exemplary embodiment of the present specification, R1 is deuterium.

According to an exemplary embodiment of the present specification, R1 is hydrogen.

According to an exemplary embodiment of the present specification, R1 is deuterium and n1 is 0.

According to an exemplary embodiment of the present specification, R1 is deuterium, and n1 is 1.

According to an exemplary embodiment of the present specification, R1 is deuterium, and n1 is 2.

According to an exemplary embodiment of the present specification, R1 is deuterium, and n1 is 3.

According to an exemplary embodiment of the present specification, R1 is deuterium, and n1 is 4.

According to an exemplary embodiment of the present specification, R1 is deuterium, and n1 is 5.

According to an exemplary embodiment of the present specification, R1 is deuterium, and n1 is 6.

According to an exemplary embodiment of the present specification, R1 is deuterium, and n1 is 7.

According to an exemplary embodiment of the present specification, R1 is deuterium, and n1 is 8.

According to an exemplary embodiment of the present specification, R1 is hydrogen and n1 is 1.

According to an exemplary embodiment of the present specification, R1 is hydrogen and n1 is 2.

According to an exemplary embodiment of the present specification, R1 is hydrogen and n1 is 3.

According to an exemplary embodiment of the present specification, R1 is hydrogen and n1 is 4.

According to an exemplary embodiment of the present specification, R1 is hydrogen and n1 is 5.

According to an exemplary embodiment of the present specification, R1 is hydrogen and n1 is 6.

According to an exemplary embodiment of the present specification, R1 is hydrogen and n1 is 7.

According to an exemplary embodiment of the present specification, R1 is hydrogen and n1 is 8.

According to an exemplary embodiment of the present specification, R2 is hydrogen or deuterium.

According to an exemplary embodiment of the present specification, R2 is hydrogen.

According to an exemplary embodiment of the present specification, R2 is deuterium.

According to an exemplary embodiment of the present specification, r2 is 7, and R2 is deuterium.

According to an exemplary embodiment of the present specification, r2 is 6, and R2 is deuterium.

According to an exemplary embodiment of the present specification, r2 is 5, and R2 is deuterium.

According to an exemplary embodiment of the present specification, r2 is 4, and R2 is deuterium.

According to an exemplary embodiment of the present specification, r2 is 3, and R2 is deuterium.

According to an exemplary embodiment of the present specification, r2 is 2, and R2 is deuterium.

According to an exemplary embodiment of the present specification, r2 is 1, and R2 is deuterium.

According to an exemplary embodiment of the present specification, the R1 is deuterium, and n1 is an integer of 1 to 8.

According to an exemplary embodiment of the present specification, the R1 is deuterium, and n1 is 8.

According to an exemplary embodiment of the present specification, R1 is hydrogen; tritium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, wherein any one of Ar1, Ar2, L1 and L2 is substituted with deuterium.

According to an exemplary embodiment of the present specification, n1 is 0, and at least one of Ar1, Ar2, L1, and L2 is substituted with deuterium.

According to an exemplary embodiment of the present specification, n1 is 0, Ar1 is Formula 2, R2 is deuterium, and r2 is an integer of 1 to 7.

According to an exemplary embodiment of the present specification, n1 is 0, Ar1 is Formula 3, R2 is deuterium, and r2 is an integer of 1 to 7.

According to an exemplary embodiment of the present specification, n1 is 0, Ar2 is Formula 2, R2 is deuterium, and r2 is an integer of 1 to 7.

According to an exemplary embodiment of the present specification, n1 is 0, Ar2 is Formula 3, R2 is deuterium, and r2 is an integer of 1 to 7.

According to an exemplary embodiment of the present specification, n1 is 0, and at least one of L1 and L2 is substituted with deuterium.

According to an exemplary embodiment of the present specification, n1 is 0, and L1 is an arylene group substituted with deuterium.

According to an exemplary embodiment of the present specification, n1 is 0, and L2 is an arylene group substituted with deuterium.

According to an exemplary embodiment of the present specification, n1 is 0, L1 and L2 are the same as or different from each other, and each independently represents an arylene group substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 is Formula 2.

According to an exemplary embodiment of the present specification, Ar1 is Formula 3.

According to an exemplary embodiment of the present specification, Ar2 is Formula 2.

According to an exemplary embodiment of the present specification, Ar2 is Formula 3.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently represented by Formula 2 or Formula 3.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are Formula 2.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are Formula 3.

According to an exemplary embodiment of the present specification, Ar1 is Formula 2, and Ar2 is Formula 3.

According to an exemplary embodiment of the present specification, Ar1 is Formula 3, and Ar2 is Formula 2.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group containing 3 to 30 carbon atoms including O or S.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group containing 3 to 20 carbon atoms including O or S.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; or a substituted or unsubstituted heterocyclic group containing 3 to 15 carbon atoms including O or S.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium; or a heterocyclic group having 3 to 30 carbon atoms including O or S unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; or a heterocyclic group having 3 to 20 carbon atoms including O or S unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group having 6 to 15 carbon atoms unsubstituted or substituted with deuterium; or a heterocyclic group having 3 to 15 carbon atoms including O or S unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted naphthyl group. phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted anthracene group, or a substituted or unsubstituted pyrene group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted naph A ethyl group, a phenanthrene group unsubstituted or substituted with deuterium, a triphenylene group unsubstituted or substituted with deuterium, an anthracene group unsubstituted or substituted with deuterium, or a pyrene group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted naphthyl group. It is a substituted phenanthrene group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted naph A ethyl group or a phenanthrene group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, 100% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 90% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 80% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 70% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 60% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 50% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 40% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 30% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 20% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 10% of all substitutable positions of Ar1 and Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 100% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 90% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 80% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 70% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 60% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 50% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 40% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 30% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 20% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 10% of all substitutable positions of Ar1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 100% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 90% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 80% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 70% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 60% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 50% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 40% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 30% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 20% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 10% of all substitutable positions of Ar2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 is Formula 2.

According to an exemplary embodiment of the present specification, Ar1 is Formula 3.

According to an exemplary embodiment of the present specification, Ar2 is Formula 2.

According to an exemplary embodiment of the present specification, Ar2 is Formula 3.

According to an exemplary embodiment of the present specification, Ar1 is Formula 2 or 3, and Ar2 is a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, or a deuterium-substituted or unsubstituted naphthyl group. , or a phenanthrene group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar2 is Formula 2 or 3, and Ar1 is a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, or a deuterium-substituted or unsubstituted naphthyl group. , or a phenanthrene group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are identical to each other.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents any one of the following substituents.

In the above substituents, the dotted line is a portion bonded to L1 or L2.

According to an exemplary embodiment of the present specification, Formula 1 may be represented by Formula 1-1 or 1-2 below.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, R1, D, L1, L2, Ar2, and n1 are as defined in Formula 1, and R2 and r2 are as defined in Formulas 2 and 3.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or an arylene group having 6 to 15 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; A divalent biphenyl group unsubstituted or substituted with heavy hydrogen; A divalent naphthyl group unsubstituted or substituted with heavy hydrogen; A divalent terphenyl group unsubstituted or substituted with heavy hydrogen; A divalent anthracene group unsubstituted or substituted with heavy hydrogen; or a divalent phenanthrene group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, 100% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 90% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 80% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 70% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 60% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 50% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 40% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 30% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 20% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 10% of all substitutable positions of L1 and L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 100% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 90% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 80% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 70% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 60% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 50% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 40% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 30% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 20% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 10% of all substitutable positions of L1 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 100% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 90% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 80% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 70% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 60% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 50% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 40% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 30% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 20% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, 10% of all substitutable positions of L2 are substituted with deuterium.

According to an exemplary embodiment of the present specification, L1 and L2 are equal to each other.

According to one embodiment of the present specification, the L1 and L2 are different from each other.

According to one embodiment of the present specification, the L1 and L2 are direct bonds.

According to an exemplary embodiment of the present specification, L1 is a direct bond, and L2 is a phenylene group substituted with deuterium.

According to an exemplary embodiment of the present specification, L1 is a direct bond, and L2 is unsubstituted phenylene.

According to an exemplary embodiment of the present specification, L2 is a direct bond, and L1 is a phenylene group substituted with deuterium.

According to an exemplary embodiment of the present specification, L2 is a direct bond, and L1 is unsubstituted phenylene.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents any one of the following substituents.

The dotted line indicates a binding site to Ar1, Ar2, and anthracene in Chemical Formula 1.

According to an exemplary embodiment of the present specification, Formula 1 is any one of the following structural formulas.

Substituents of the compound of Formula 1 may be combined by a method known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

In addition, by introducing various substituents into the core structure of the above structure, compounds having inherent characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, and electron transport layer materials used in the manufacture of organic light emitting devices into the core structure, materials satisfying the requirements of each organic layer can be synthesized. can

In addition, the organic light emitting device according to the present invention includes a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers contains the aforementioned compound.

The organic light emitting device of the present invention may be manufactured by conventional organic light emitting device manufacturing methods and materials, except for forming one or more organic material layers using the above compounds.

The compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a hole injection and hole transport layer simultaneously, a light emitting layer, an electron transport layer, an electron injection layer, and the like as organic material layers. However, the structure of the organic light emitting diode is not limited thereto and may include a smaller number of organic material layers or a larger number of organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously injects and transports electrons, and at least one of the layers is represented by Chemical Formula 1. compounds may be included.

In another organic light emitting device, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer may include the compound represented by Chemical Formula 1.

In the organic light emitting device of the present invention, the organic material layer may include at least one of a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes, and at least one of the layers is represented by Chemical Formula 1. compounds may be included.

In another organic light emitting device, the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or hole injection layer may include the compound represented by Chemical Formula 1.

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1.

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1 as a host.

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1 as a host and may further include additional materials.

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1 as a host and may further include a dopant material.

In the organic light emitting device of the present invention, the light emitting layer includes a host and a dopant in a weight ratio of 99:1 to 1:99.

In the organic light emitting device of the present invention, the light emitting layer includes a host and a dopant in a weight ratio of 80:1 to 50:50.

In the organic light emitting device of the present invention, the light emitting layer includes a host and a dopant in a weight ratio of 50:1 to 50:50.

In the organic light emitting device of the present invention, the light emitting layer includes a host and a dopant in a weight ratio of 30:1 to 10:1.

In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

(1) anode/hole transport layer/light emitting layer/cathode

(2) anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

(7) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(8) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

(9) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(11) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(12) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(13) anode/hole injection layer/hole transport layer/electron blocking layer/emission layer/electron transport layer/electron injection layer/cathode

(14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(15) anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode

(16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(18) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron injection and transport layer / cathode

The structure of the organic light emitting device of the present invention may have a structure shown in FIG. 1, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1. In this structure, the compound represented by Chemical Formula 1 may be included in the organic material layer 3.

The structure of the organic light emitting diode of the present invention may have a structure shown in FIG. 2, but is not limited thereto.

2 shows a substrate 1 on a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9, electron injection and A structure of an organic light emitting device in which the transport layer 10 and the second electrode 4 are sequentially stacked is illustrated. In this structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer 8 .

For example, the organic light emitting device according to the present invention uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, and from the group consisting of a hole injection layer, a hole transport layer, a hole transport and hole injection layer, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons thereon. After forming an organic material layer including one or more selected layers, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer can be formed by a solvent process other than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method. Can be made in layers.

The anode is an electrode for injecting holes, and a material having a high work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and it is preferable that the cathode material is a material having a small work function so as to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage, HOMO (highest occupied molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristic from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There are advantages to avoiding this.

According to an exemplary embodiment of the present specification, the hole injection layer includes a compound represented by Chemical Formula HI-1, but is not limited thereto.

[Formula HI-1]

In the above formula HI-1,

L301 to L303 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R301 to R303 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, R301 to R303 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R301 to R303 are the same as or different from each other, and each independently a substituted or unsubstituted carbazole group; A substituted or unsubstituted phenyl group; biphenyl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, the L301 to L303 are the same as or different from each other, and are each independently directly bonded; Arylene group; or a heteroarylene group.

According to an exemplary embodiment of the present specification, Formula HI-1 is represented by the following compound.

The hole transport layer may play a role of facilitating hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by Formula HT-2, but is not limited thereto.

[Formula HT-2]

In the above formula HT-2,

R315 to R317 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring,

r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other;

r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more of R316 are the same as or different from each other.

According to an exemplary embodiment of the present specification, R317 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R317 is a substituted or unsubstituted carbazole group; A substituted or unsubstituted phenyl group; biphenyl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, Formula HT-2 is represented by the following compound.

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may use the aforementioned spiro compound or a material known in the art.

According to an exemplary embodiment of the present specification, the electron blocking layer includes a compound represented by Chemical Formula EB-1, but is not limited thereto.

[Formula EB-1]

In the above formula EB-1,

L311 to L313 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R311 to R313 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, R311 to R313 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R311 to R313 are the same as or different from each other, and each independently a substituted or unsubstituted carbazole group; A substituted or unsubstituted phenyl group; biphenyl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, the L311 to L313 are the same as or different from each other, and are each independently directly bonded; Arylene group; or a heteroarylene group.

According to an exemplary embodiment of the present specification, Formula EB-1 is represented by the following compound.

The light emitting layer may emit red, green or blue light and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

A host material for the light emitting layer includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

When the light emitting layer emits red light, PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) iridium) are used as light emitting dopants. ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum), but is not limited thereto. When the light emitting layer emits green light, a phosphorescent material such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the light emitting dopant. However, it is not limited thereto. When the light emitting layer emits blue light, as the light emitting dopant, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.

According to an exemplary embodiment of the present specification, the dopant is represented by a compound represented by Chemical Formula D-2.

[Formula D-2]

In the above formula D-2,

T1 to T5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group,

t3 and t4 are each an integer from 1 to 4,

t5 is an integer from 1 to 3;

When t3 is 2 or more, the two or more T3s are the same as or different from each other,

When t4 is 2 or more, the two or more T4s are the same as or different from each other,

When t5 is 2 or more, the two or more T5s are the same as or different from each other.

According to an exemplary embodiment of the present specification, the T1 to T5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the T1 to T5 are the same as or different from each other, and each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the T1 to T5 are the same as or different from each other, and each independently hydrogen; methyl group; tert-butyl group; diphenylamine group; or a phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group.

According to an exemplary embodiment of the present specification, Formula D-2 is represented by the compound below.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer may serve to facilitate electron transport. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing deterioration of electron transport properties, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in driving voltage to improve electron movement. There are advantages that can be

According to an exemplary embodiment of the present specification, the electron transport layer includes a compound represented by Chemical Formula ET-1, but is not limited thereto.

[Formula ET-1]

In the above formula ET-1,

At least one of Z11 to Z13 is N and the others are CH,

L601 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar601 and Ar602 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

l601 is an integer from 1 to 5, and when l601 is 2 or more, the two or more L601s are the same as or different from each other.

According to an exemplary embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L601 is a phenylene group; a biphenylylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

According to an exemplary embodiment of the present specification, Formula ET-1 is represented by the following compound.

The electron injection layer may serve to smoothly inject electrons. The electron injecting material has the ability to transport electrons, has an excellent electron injecting effect from the cathode, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , compounds having excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. and their derivatives, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.

The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

The organic light emitting device of the present invention may be manufactured by conventional organic light emitting device manufacturing methods and materials, except for forming one or more organic material layers using the above compounds.

The preparation method of the compound of Chemical Formula 1 and the manufacture of an organic light emitting device using the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

In the reaction scheme below, various kinds of intermediates can be synthesized according to the appropriate selection of starting materials known to those skilled in the art for the type and number of substituents. Reaction type and reaction conditions may be used those known in the art.

All of the compounds represented by Chemical Formula 1 described herein can be prepared by appropriately combining the preparation formulas described in the examples herein and the intermediates based on common technical knowledge.

<Production Example 1>

One) Synthesis of Compound 1

4-(10-bromoantracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]thiophene 5,5-dioxide in a 500 mL round bottom flask under a nitrogen atmosphere. -1,2,3,6,7,8,9-d7 (5.50 g, 11.31 mmol) and compound a-1 (3.92 g, 13.57 mmol) were completely dissolved in 240 mL of tetrahydrofuran, followed by a 2M aqueous solution of potassium carbonate. (120 mL) was added, and after adding tetrakis-(triphenylphosphine)palladium (0.65 g, 0.57 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 mL of toluene to prepare Compound 1 (3.56 g, yield: 55%).

MS[M+H] ⁺ = 569

<Production Example 2>

One) Compound synthesis of compound 2 below

Compound 2-(10-bromoantracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]thiophene 5,5- Dioxide (5.50 g, 11.48 mmol) and compound a-2 (3.99 g, 13.78 mmol) were completely dissolved in 240 mL of tetrahydrofuran, 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(triphenylphosate) Pin) After adding palladium (0.66 g, 0.57 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of toluene to prepare Compound 2 (4.13 g, yield: 64%).

MS[M+H] ⁺ = 561

<Production Example 3>

One) Compound synthesis of compound 3 below

Compound 2-(10-bromoantracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]thiophene 5,5- After completely dissolving dioxide-1,3,4,6,7,8,9-d7 (5.50 g, 11.32 mmol) and compound a-3 (3.54 g, 13.58 mmol) in 240 mL of tetrahydrofuran, 2M potassium carbonate Aqueous solution (120 mL) was added, and after adding tetrakis-(triphenylphosphine)palladium (0.65 g, 0.57 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare compound 3 (3.57 g, yield: 58%).

MS[M+H] ⁺ = 541

<Production Example 4>

One) Compound synthesis of compound 4 below

Compound 2-(10-bromoantracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]thiophene 5,5- Dioxide (5.50 g, 11.48 mmol) and compound a-4 (3.50 g, 13.78 mmol) were completely dissolved in 240 mL of tetrahydrofuran, 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(triphenylphos) Pin) After adding palladium (0.66 g, 0.57 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of toluene to prepare Compound 4 (3.39 g, yield: 56%).

MS[M+H] ⁺ = 527

<Production Example 5>

One) Compound synthesis of compound 5 below

Compound 2-(10-bromoantracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]thiophene 5,5- After completely dissolving dioxide-1,3,4,6,7,8,9-d7 (5.50 g, 11.32 mmol) and compound a-5 (4.13 g, 13.58 mmol) in 240 mL of tetrahydrofuran, 2M potassium carbonate Aqueous solution (120 mL) was added, and after adding tetrakis-(triphenylphosphine)palladium (0.65 g, 0.57 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare Compound 5 (4.03 g, yield: 61%).

MS[M+H] ⁺ = 584

<Production Example 6>

One) Compound synthesis of compound 6 below

Compound 4-(10-bromoantracen-9-yl)dibenzo[b,d]thiophene 5,5-dioxide-1,2,3,6,7,8,9-d7 ( After completely dissolving 5.50 g, 11.51 mmol) and compound a-6 (4.56 g, 13.81 mmol) in 240 mL of tetrahydrofuran, a 2M aqueous solution of potassium carbonate (120 mL) was added, and tetrakis-(triphenylphosphine) After adding palladium (0.66 g, 0.58 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of ethyl acetate to prepare compound 6 (3.88 g, yield: 56%).

MS[M+H] ⁺ = 602

<Production Example 7>

One) Compound synthesis of compound 7 below

2-(10-bromoantracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]thiophene 5,5-dioxide in a 500 mL round bottom flask under a nitrogen atmosphere. (5.50 g, 11.48 mmol) and compound a-7 (4.55 g, 13.78 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and 2M potassium carbonate aqueous solution (120 mL) was added thereto, and tetrakis-(triphenylphosphine) ) After adding palladium (0.66 g, 0.57 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of toluene to prepare compound 7 (4.19 g, yield: 66%).

MS[M+H] ⁺ = 553

<Production Example 8>

One) Synthesis of compound 8 below

Compound 2-(10-bromoantracen-9-yl)dibenzo[b,d]thiophene 5,5-dioxide (5.50 g, 11.68 mmol), and compound a-8 (4.78 g, 14.01 mmol) was completely dissolved in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.67 g, 0.58 mmol) was added, and heating and stirring were performed for 6 hours. did The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of toluene to prepare Compound 8 (5.07 g, yield: 72%).

MS[M+H] ⁺ = 606

<Production Example 9>

One) Compound synthesis of compound 9

Compound 2-(10-bromoantracen-9-yl)dibenzo[b,d]thiophene 5,5-dioxide (5.50 g, 11.68 mmol), and compound a-9 (4.78 g, 14.01 mmol) was completely dissolved in 240 mL of tetrahydrofuran, 2M potassium carbonate aqueous solution (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.67 g, 0.58 mmol) was added, and heating and stirring were performed for 4 hours. did The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare compound 9 (4.98 g, yield: 70%).

MS[M+H] ⁺ = 606

<Production Example 10>

1) Synthesis of compound 10 below

4-(10-bromoantracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]thiophene 5,5-dioxide in a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving -1,2,3,6,7,8,9-d7 (5.50 g, 11.68 mmol) and compound a-10 (4.78 g, 14.01 mmol) in 240 mL of tetrahydrofuran, a 2M aqueous solution of potassium carbonate (120 mL) was added, and after adding tetrakis-(triphenylphosphine)palladium (0.67 g, 0.58 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 mL of toluene to prepare Compound 10 (4.55 g, yield: 65%).

MS[M+H] ⁺ = 621

<Production Example 11>

One) Compound synthesis of compound 11

Compound 2-(4-(10-bromoantracen-9-yl-1,2,3,4,5,6,7,8-d8)phenyl)dibenzo[b,d] in a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving thiophene 5,5-dioxide (5.50 g, 9.89 mmol) and compound a-11 (2.48 g, 11.87 mmol) in 240 mL of tetrahydrofuran, 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis After adding -(triphenylphosphine)palladium (0.57 g, 0.49 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare Compound 11 (3.88 g, yield: 70%).

MS[M+H] ⁺ = 558

<Production Example 12>

1) Synthesis of Compound 12

Compound 4-(4-(10-bromoantracen-9-yl-1,2,3,4,5,6,7,8-d8)phenyl)dibenzo[b,d] in a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving thiophene 5,5-dioxide (5.50 g, 9.89 mmol) and compound a-12 (3.10 g, 11.87 mmol) in 240 mL of tetrahydrofuran, 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis After adding -(triphenylphosphine)palladium (0.57 g, 0.49 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare Compound 12 (4.24 g, yield: 70%).

MS[M+H] ⁺ = 610

Example 1-1

A glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

A hole injection layer was formed by thermally vacuum-depositing the compound HI1 and the compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the ITO transparent electrode prepared as described above. A hole transport layer was formed by vacuum depositing a compound (1150 Å) represented by Chemical Formula HT1 on the hole injection layer. Subsequently, an electron blocking layer was formed by vacuum depositing a compound of EB1 to a film thickness of 50 Å on the hole transport layer. Subsequently, Compound 1 synthesized in Preparation Example 1 and the compound represented by the following Chemical Formula BD were vacuum deposited on the electron blocking layer to a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer. A hole blocking layer was formed on the light emitting layer by vacuum depositing a compound of HB1 to a film thickness of 50 Å. Subsequently, a compound represented by Chemical Formula ET1 and a compound represented by Chemical Formula LiQ were vacuum deposited at a weight ratio of 1:1 on the hole-blocking layer to form an electron injection and transport layer having a thickness of 310 Å. A negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å / sec, the deposition rate of lithium fluoride on the cathode was 0.3Å / sec, and the deposition rate of aluminum was 2Å / sec, and the vacuum level during deposition was 2ⅹ10 ^-7 ~ Maintaining 5x10 ^-6 torr, an organic light emitting device was manufactured.

Examples 1-2 to 1-10

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of the compounds of Preparation Example 1.

Comparative Examples 1-1 to 1-5

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of the compounds of Preparation Example 1. The compounds of BH1 to BH5 used in Table 1 are as follows.

Experimental Example 1

When current was applied to the organic light emitting devices prepared in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 means the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(light emitting layer) Voltage
(V@10mA
/cm ² ) efficiency
(cd/A@10mA
/cm ² ) color coordinates
(x,y) T95
(hr) Example 1-1 compound 1 4.33 6.53 (0.147, 0.045) 315 Example 1-2 compound 2 4.35 6.56 (0.146, 0.046) 295 Examples 1-3 compound 3 4.34 6.57 (0.145, 0.045) 315 Example 1-4 compound 4 4.32 6.55 (0.146, 0.047) 285 Example 1-5 compound 5 4.33 6.59 (0.147, 0.045) 295 Example 1-6 compound 6 4.31 6.58 (0.146, 0.06) 275 Examples 1-7 compound 7 4.34 6.56 (0.145, 0.045) 280 Examples 1-8 compound 8 4.30 6.59 (0.147, 0.047) 270 Examples 1-9 compound 9 4.31 6.33 (0.146, 0.046) 275 Examples 1-10 compound 10 4.33 6.41 (0.147, 0.046) 280 Comparative Example 1-1 BH1 4.49 6.19 (0.146, 0.045) 205 Comparative Example 1-2 BH2 4.51 6.14 (0.146, 0.047) 210 Comparative Example 1-3 BH3 5.11 5.52 (0.145, 0.046) 85 Comparative Example 1-4 BH4 5.26 5.76 (0.147, 0.046) 150 Comparative Example 1-5 BH5 5.57 5.45 (0.147, 0.045) 95

As shown in Table 1, the organic light emitting device using the compound of the present invention as a light emitting layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.

In Examples 1-1 to 1-10, the organic light emitting devices using the compounds of the present invention have lower voltage, higher efficiency and longer lifespan than the organic light emitting devices of Comparative Examples 1-1 to 1-5 prepared using materials of BH1 to BH5. showed the characteristics of

In particular, Comparative Examples 1-1 to 1-3 using compounds without deuterium in anthracene have shorter lifespans than Examples 1-1 to 1-10. In particular, looking at Comparative Example 1-2, even if the substitution position of Ar1 is the same as that of the present invention, it can be confirmed that the lifetime is shorter than that of Examples 1-1 to 1-10.

In Comparative Examples 1-4 and 1-5, Ar1 is different from the compound represented by Formula 1 herein, and in this case, it can be confirmed that there is a large difference in voltage and lifetime.

Although the preferred embodiment (light emitting layer) of the present invention has been described above, the present invention is not limited thereto, and it is possible to carry out various modifications within the scope of the claims and detailed description of the invention, and this is also the scope of the invention. belong to the category

1: substrate
2: anode
3: organic material layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electronic blocking layer
8: light emitting layer
9: hole blocking layer
10: electron injection and transport layer

Claims (12)

A compound of Formula 1:
[Formula 1]

In Formula 1,
R1 is hydrogen; heavy hydrogen; tritium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
n1 is an integer from 0 to 8;
When n1 is 2 or more, R1 are the same as or different from each other,
L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing O or S,
At least one of Ar1 and Ar2 is of Formula 2 or 3 below,
[Formula 2]

[Formula 3]

In Formulas 2 and 3,
The dotted line is the part connected to L1 or L2,
R2 is hydrogen; heavy hydrogen; tritium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted heterocyclic group containing O or S,
r2 is an integer from 0 to 7, and when r2 is 2 or more, R2 are the same as or different from each other;
n1 is 0, or both R1 are hydrogen; tritium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or when it is a substituted or unsubstituted heterocyclic group, at least one of Ar1, Ar2, L1 and L2 is substituted with deuterium. The phosphorus compound according to claim 1, wherein R1 is deuterium and n1 is 8. The compound according to claim 1, wherein Ar1 is of Formula 2. The compound according to claim 1, wherein Ar1 is of Formula 3. The method according to claim 1, wherein Ar1 is represented by Formula 2 or 3, and Ar2 is a phenyl group unsubstituted or substituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, a naphthyl group unsubstituted or substituted with deuterium, or a deuterium substituted or unsubstituted naphthyl group. A compound that is a substituted or unsubstituted phenanthrene group. The method according to claim 1, wherein the L1 and L2 are the same as or different from each other, each independently a direct bond; Or a compound that is an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen. The method according to claim 1, wherein Ar2 is represented by Formula 2 or 3, and Ar1 is a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted naphthyl group, or a deuterium-substituted or unsubstituted naphthyl group. A compound that is a substituted or unsubstituted phenanthrene group. The compound according to claim 1, wherein r2 is 7, and R2 is deuterium. The compound of claim 1, wherein Formula 1 is any one of the following structural formulas:

a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 9. . The organic light emitting device of claim 10, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound. The organic light emitting device of claim 10, wherein the emission layer includes the compound represented by Chemical Formula 1 as a host and an organic compound or metal complex as a dopant.

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